Hans jordan



Patented July 20, 192 6 UNITED STATES PATENT OFFICE.

EARS J'OBDKN,OF BERLIN-STEGLITZ, GERMANY, ASSIGNOR TO THE FIRM: CHEHISOHE FABBIK AUF ACTIEN (VORM. E. scnnnmo), or BERLIN, GERMANY.

nmYnnoxY nrrnnm ncnzrsrrann comrounns.

Io Drawing. Application filed September 8, 1925, Serial No. 55,153, and in Germany September 20, 1924.

My invention refers to new chemical products and to the process of making same.

corresponding to the formula HO OH H\ H: E

wherein R and R can-be either two identical or two difierent alkyl or aryl radicals.

The term phenyl is meant to comprise also 1 the ortho-alkyl substitution products of phenol such as for instance orthocresol, so that the above formula is meant to comprlse also compounds corresponding to the formula nical'andtherapeutical uses. They are prepared by acting with hydrogen in the presence of a catalyst on condensation products from ketones and phenols (incl. the ortho alkyl substitution products of phenols) until 12 atoms of hydrogen have enteredinto combination. As'a catalyst I employ for instance nickel, colloidal palladium or platinum black. v

In practising my invention I may pro ceed for instance as follows:

Emample ing at 102-106 under 12 mms. pressure and having the scent of lilies of-the-valley.

The comparatively wide range of boiling points results from the formation of 3 isomers which can be separated from each other by repeated, very careful fractional distillation.- These 3 isomers, one of which has the character of a cis-cis, the second of a cis-trans and the third of a trans-trans compound, can be illustrated by the following formulae H H H on on on no on H0 H n n o c c H c H c n 015.018 0 c elk trans trails-trans in which all unimportant details are left out. Example 2.

100 parts by weight of 4-dihydroxy-3-dimethyl diphenyl dimethyl methane (see page 24 of Unverza s dissertation published in 1904 at arburg and entitled: Ueber die Einwirkung von' Brom auf Dipara-oxytolyl-dimethylmethan) are treated with hydrogen under pressure in an-autoclave at 150170 in the presence of 2-5 parts of a nickel catalyst, until 12 atoms of hydrogen have entered into combination.

The compound formed, viz di-l-hydroxy-Elmethyl cyclohexanyl dimethyl met ane, is a viscous, limpid oil boiling at 108-112 un-.

der 12 mms. pressure and havin a very agreeable scent resembling hyacinfiis. The comparatively Wide range of boiling temperaturesis the result of the formation of cis-trans isomers, 10 of which can form theoretically.

By careful fractional distillation I have been able to obtain fractions which contain a high percentage of some of these isomers.

Example 3.

100 parts by weight of the condensation product of methyl ethyl ketone with henol (Berichte der Deutschen Chemischen esellschaft vol. 25, page 334, abstracts) are treated in the presence of 2-5 parts ofa nickel catalyst with hydro en under pressure until 12 atom of hydrogen have entered into combination. The roduct formed is di-4-hydroxy cyclohexany methyl ethyl methane, being a viscous oil having an agreeable, flowery smell which consists of a mixture of difl'erent stereo isomers and boils at 120125 C. under 14 mms. pressure.

I Wish it to be understood that the production of the new compounds is not limited to the exact proportions and operations described, for obvious modifications will ocour to a person skilled in the art.

I claim e v 1. As a new product, a hydrogenated dihydroxy diphenyl methane compound corresponding to the formula H, HI

no on H- H! n wherein the ortho-positions relative to the h droxyl group can also be taken up bya kyl radicals.

3. As a new product, a di-4-hydroxy-3- methyl cyclo hexan l dimethyl methane corresponding to the rmula CH; H

CH H

4. The process of roducing hydrogenated dihydr xy dipheny compriging acting with hydrogen in the methane compounds presence of a catalyst on a condensation product from a ketone and a henol until 12 hydrogen atoms have entere into combination.

5. The process of producing hydrogenated dihydroxy diphenyl methane compounds comprising acting with hydrogen in the presence of a catalyst on a condensation product from acetone and a phenol, until 12 hydrogen atoms have entered into combination.

6. The process of roducing hydrogenated dihydroxy dipheny methane compounds comprising acting with hydrogen in the presence of a catalyst on a condensation product from acetone and ortho cresol, until 12 hydrogen atoms have entered into combination.

7. The process of producing hydrogenated dihydroxy diphenyl methane compounds comprising acting with hydrogen 111 the presence of a nickel catalyst under pressure at a tem rature of 150170 on a condensation pro not from acetone and ortho cresol, until 12 atoms of hydrogen have entered into combination.

In testimony whereof I aflix my signature. 

